An LA-based animator, reeling from heartbreak, is pushed back into the dating world by his well-meaning friends. When he meets an emotionally intuitive record exec who matches his particular brand of weird, they take a spontaneous road trip along the California coast, including stops throughout SLO County and a stay at the iconic Madonna Inn. As they confront lingering pasts, HOW TO DATE AGAIN embraces the messiness of healing, vulnerability, and choosing connection.

Cast

Haley Joel Osment

Hugh

Natasha Loring

Leigh

Johnno Wilson

Xander

Amanda Payton

Kai

Kevin Nealon

Larry

Emilio Rivera

Rancher